Physical and chemical properties of 3-Bromothiophene

Product identification

EINECS NO.: 212-821-3
Formula: C4H3BrS
Formula weight : 163.03
H.S. CODE 2934.99
Synonyms: 3-Thienyl bromide; beta-Bromo3-Bromothiophene;

Physical and chemical proper

Physical state: 3-Bromothiophene is clear to pale yellow liquid
Melting point < -10 C
Boiling point: 157 - 158 C
Specific gravity : 1.72 - 1.74
Solubility in water: immiscible 
Refractive index: 1.5863
Flash point: 56 C
Stability Stable: under ordinary conditions
CAS NO. : 872-31-1

3-Bromothiophene, also known as thiofuran, is a cyclic compound containing four carbon atoms and one sulfur atom in the ring. It is an analog to furan and pyrrole where the sulfur atom is replaced by O and NH respectively. It is a toxic, flammable, and colorless liquid; insoluble in water (soluble in most organic solvents including alcohol and ether); melting at -38 C, boiling at 84 C.

3-Bromothiophene is the simplest aromatic compound containing sulfur atom and it shares some similar chemical properties with benzene. The lone electron pairs on sulfur in the delocalized pi electron system does not exhibits the properties of thioethers but aromaticity. The sulfur atom is unreactive but the adjacent carbons are susceptible to attack by electrophiles. It is reactive toward sulfonation.

In commercial 3-Bromothiophene can be prepared by the reaction of butane and sulfur. 3-Bromothiophenes are also prepared by the reaction of diketones with Lawesson's reagent. This chemical and its derivatives exist in petroleum or coal. It derivatives are also found in natural plant pigments. Biotin, a water-soluble B-complex vitamin, is a reduced 3-Bromothiophene derivative. 3-Bromothiophene moiety is found in ccphalothin antiboitics.

3-Bromothiophene is used as a solvent and chemical intermediate. Its derivatives are used in manufacturing dyes, aroma compounds and pharmaceuticals. They are used as monomers to make condensation copolymers. Organic conductive polymers are responsible for the important materials science for the application of polymer electro luminescence.

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History of Ofloxacin

Ofloxacin is an antibiotic that is used to treat bacterial infections. It belongs to the fluoroquinolone class of antibiotics which includes levofloxacin (Levaquin), ciprofloxacin (Cipro), gatifloxacin (Tequin), norfloxacin (Noroxin), moxifloxacin (Avelox), trovafloxacin (Trovan) and others. Ofloxacin stops the multiplication of bacteria by inhibiting the reproduction and repair of their genetic material (DNA). The FDA approved ofloxacin in December 1990.

Ofloxacin(CAS NO:82419-36-1) was developed as a broader-spectrum analog of norfloxacin, the first fluoroquinolone antibiotic, it was first patented in 1982 (European Patent Daiichi) and received U.S. Food and Drug Administration (FDA) approval December 28, 1990. One of the first major adverse reactions noted with Ofloxacin were psychiatric in nature. It can cause serious psychiatric side effects with up to 25% of such patients suffering such reactions. This reaction was detailed within Stephen Fried’s 1999 book: “Bitter Pills”

In the United States name branded ofloxacin is rarely used anymore, having been discontinued by the manufacturer, Ortho-McNeil-Janssen, a subsidiary of Johnson & Johnson Johnson and Johnson's annual sales of Floxin in 2003 was approximately $30 million, whereas their combined sales of Levaquin/Floxin exceeded $ 1.15 billion in the same year. However generic use continues. The FDA website lists Floxin (Ortho McNeil Jannsen) as being discontinued, with just a few generic equivalents still in use. The otic solution continues to be listed as being available both as an original drug as well as a generic equivalent.

Oral and I.V. Floxin is not licensed by the FDA for use in children due to the risk of serious reversible and irreversible injury to the musculoskeletal system. Other fluoroquinolones do have a limited licensed uses in children but are generally not recommended due to safety concerns. Ofloxacin (and its derivatives) has also been associated with a few isolated reports of unexplained pediatric fatalities. Children (those under 18) are also at an increased risk of bone, joint, or tendon toxicities.

Prescribing ofloxacin in the absence of a proven or strongly suspected bacterial infection or a prophylactic indication is unlikely to provide benefit to the patient and increases the risk of the development of severe adverse drug reactions.

In the adult population ofloxacin is limited to the treatment of proven serious and life threatening bacterial infections such as:
1.Acute bacterial exacerbations of chronic bronchitis
2.Community-acquired pneumonia
3.Uncomplicated skin and skin structure infections
4.Nongonococcal urethritis and cervicitis
5.Mixed Infections of the urethra and cervix
6.Acute pelvic inflammatory disease
7.Uncomplicated cystitis
8.Complicated urinary tract infections
9.Prostatitis
10.Acute, uncomplicated urethral and cervical gonorrhea.

Ofloxacin has not been shown to be effective in the treatment of syphilis. Floxin is now considered to be contraindicated for the treatment of certain sexually transmitted diseases by some experts due to bacterial resistance.

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How to take Clofarabine

Clofarabine belongs to the group of medicines known as antineoplastics. It is used to treat a type of cancer of the white blood cells called acute lymphoblastic leukemia (ALL) in patients 1 to 21 years of age who have already used at least two other cancer medicines.

Clofarabine interferes with the growth of cancer cells, which are eventually destroyed. Since the growth of normal body cells also may be affected by clofarabine, other effects also occur. Some of these effects may be serious and must be reported to your doctor.

Before you begin treatment with clofarabine(CAS NO:123318-82-1), you and your doctor should talk about the good this medicine will do as well as the risks of using it. It is to be administered only by or under the immediate supervision of your doctor. So let me show you how it is given and what possible side effects it may have?

How it is given

Clofarabine is given as a drip (infusion) that usually takes about two hours. It's given in one of the following ways:
1.through a fine tube inserted into a vein, usually in the back of the hand (cannula)
2.through a fine, plastic tube inserted under the skin and into a vein near the collarbone (central line)
3.into a fine tube inserted into a vein in the crook of the arm (PICC line)
4.into a small port placed under the skin below the collarbone (Implantable ports).

Your doctor or specialist nurse will explain more about this to you. Chemotherapy is usually given as a course of several sessions (or cycles) of treatment over a few months. Clofarabine is usually given every day for five days, and repeated every 2-6 weeks. The nurse or doctor will discuss your treatment plan with you and your child.

Before your child begins treatment, their doctor will arrange for them to have blood tests. They will usually be given anti-sickness drugs before and/or during their treatment.

Possible side effects

Tumor lysis syndrome (TLS). Clofarabine quickly kills leukaemia cells in the blood. The body may react to this. Signs include hyperkalemia, hyperuricemia, and hyperphosphatemia. TLS is very serious and can lead to death if it is not treated right away.

2,Systemic Inflammatory Response Syndrome (SIRS): Symptoms include fast breathing, fast heartbeat, low blood pressure, and fluid in the lungs.

3.Bone marrow problems (suppression). Clofarabine can stop the bone marrow from making enough red blood cells, white blood cells, and platelets. Serious side effects that can happen because of bone marrow suppression include severe infection (sepsis), bleeding, and anemia.
Effects on pregnancy and breastfeeding. Girls and women should not become pregnant or breastfeed during treatment which may harm the baby.

Dehydration and low blood pressure. Clofarabine can cause vomiting and diarrhea which may lead to low body fluid (dehydration). Signs and symptoms of dehydration include dizziness, lightheadedness, fainting spells, or decreased urination.

5.Other side effects. The most common side effects are stomach problems (including vomiting, diarrhea, and nausea), and effects on blood cells (including low red blood cells count, low white blood cell count, low platelet count, fever, and infection. Clofarabine can also cause tachycardia and can affect the liver and kidneys.

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What should be careful about Tacrolimus overdose

Tacrolimus lowers your body's immune system. The immune system helps your body fight infections. The immune system can also fight or "reject" a transplanted organ such as a liver or kidney. This is because the immune system treats the new organ as an invader. 

Tacrolimus is used together with other medicines to prevent your body from rejecting a heart, liver, or kidney transplant. It may also be used for purposes not listed in this medication guide. But it is possible for someone to use too much tacrolimus(CAS NO:104987-11-3). The overdose effects will vary, based on certain factors. Possible symptoms include hives, tremors, and kidney problems. Treatment will typically involve supportive care to treat any symptoms that occur as a result of the overdose, in addition to pumping the stomach.

Treatment for a Tacrolimus Overdose

The treatment for an overdose of tacrolimus may vary. If the overdose was recent and taken by mouth, a healthcare provider may "pump the stomach" to help reduce the amount of the drug absorbed into the bloodstream. Dialysis is not expected to be helpful for removing tacrolimus from the bloodstream.

Treatment will also include supportive care, which consists of treating the symptoms that occur as a result of the overdose. For example, supportive treatment for a tacrolimus overdose may include:

Fluids through an intravenous line (IV), if necessary
Close monitoring of kidney function, body salts (electrolytes), and blood pressure
Medications to treat high blood pressure, if needed.

It is important that you seek medical attention immediately if you believe that you or someone else may have overdosed on this medication.

Effects of an Overdose

There have been reports of overdoses of up to 30 times the recommended tacrolimus dose. Based on these cases, possible overdose symptoms may include but are not limited to:
Tremors
Kidney problems
High blood pressure (hypertension)
Swelling (edema) of the arms, hands, legs, ankles, or feet
Hives
Loss of energy.

These symptoms are unlikely to occur from a tacrolimus ointment overdose, however, as very little of the medicine is absorbed through the skin into the bloodstream. Using too much tacrolimus ointment could cause skin irritations, such as redness, stinging, burning, and itching. If large amounts of the ointment are taken by mouth, overdose symptoms also could occur.

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Discussions on the experiment of 3-Methyl-1-phenyl-2-pyrazolin-5-one

Results of the experiment 

There were infarcted lesions on the irradiated sensorimotor cortex the day after the infarction and 7 days after the infarction. The infarction area after 7 days was smaller in the edaravone-treated group. The infarcted area 1 day after the infarction was 20.9±4.90(mean±standard error of the mean (SE)) mm2 in the 3-Methyl-1-phenyl-2-pyrazolin-5-one treated group and 27.2±8.20 mm2 in the control group. There was no significant difference between these groups. 

Seven days after the infarction, the area of infarction was 17.4±1.39 mm2 in the edaravone group and 33.3±2.66 mm2 in the control group. There was a significant difference between these groups. The recovery of paralysis in the 3-Methyl-1-phenyl-2-pyrazolin-5-one(CAS NO:89-25-8) treated group was significantly earlier than in the untreated group. After 7 days, both groups were mostly recovered with scores of 7 . 

The scores for the beam walking test were 4.2  ±0.29 on day 1 after infarction, 6.5±0.2 on day 2, 6.93±0.06 on day 3, and 7.00 ±0.00 on day 4. However, the mean scores were 2.4 ±0.32 on day 1, 4.75±0.42 on day 2, 5.7±0.42 on day 3, 6.3±0.30 on day 4, 6.15±0.39 on day 5, 6.55±0.21 on day 6, and 6.6±0.21 on day 7.

The discussion on the results

Free radicals gradually increase in the areas surrounding the ischemic area, including the penumbra, and they rapidly increase after reperfusion. OPC-14117, NXY-097, and other free radical scavengers have been previously examined. However, clinical applications of these have not been done, except with 3-Methyl-1-phenyl-2-pyrazolin-5-one.

Abe et al. have conducted basic research on 3-Methyl-1-phenyl-2-pyrazolin-5-one, and it was approved as a brain protection drug in 2001 in Japan. It has a protective effect on oxidative injuries in the brain by eliminating free radicals. It has been widely used in Japan in acute patients with cerebral thromboses and cerebral embolisms. There have been reports that edaravone has protective effects on lacunar infarctions in clinical patients. A recent study has reported that the administration of 3-Methyl-1-phenyl-2-pyrazolin-5-one with cilostazol had more protective effects. In order to increase blood flow and diminish free radicals, the coadministration of tissue plasminogen activator and edaravone or edaravone injections after the administration of tissue plasminogen activator have been shown to be effective in a clinical study.

Most animal studies utilize rat embolic models or reperfusion models. Besides rat models, rabbit models have also been reported. However, the rabbit models were embolic models. There have been few reports on the time course of the function of the extremities. Nishi et al. have evaluated rat activity with 5-grade scores, but a time-course study was not done. Kawai et al. have evaluated hemiplegic rats with a 4-step qualitative analysis of abnormal postures when hanging by the tail. However, the time course was not evaluated. Jin et al. have evaluated the survival rate, neuronal survival, and blood flow after the simultaneous administration of argatroban and 3-Methyl-1-phenyl-2-pyrazolin-5-one in Meriones unguiculatus. This report was also silent about physical activities.

Recently, Lu et al. have reported the effects of 3-Methyl-1-phenyl-2-pyrazolin-5-one on cognitive function that was evaluated by a maze test in a transient global ischemia model. There was early improvement in the edaravone-administered group, and the results were compatible with our results. Zhang et al. have reported the effects of this chemical according to infarction size and improvements in physical activity. These findings were also compatible with our results.

We studied the effects of this chemical in a rat model of photochemically induced infarction. There have been no reports concerning the effects of this chemical in a model of photochemically induced infarction. The distinctive feature of this model was that we were able to obtain similar infarction sizes and locations. It was presumed that the ischemic changes were similar to those of cerebral thrombosis and that we were able to compare it with other cerebral embolism models, because a thrombus was formed in the irradiated area of the cortex.

In our results, the infarcted areas were not significantly different between the edaravone-treated group and the control group the day after the infarction. However, the infarcted area in the edaravone group was about half of the size of that in the control group. The infarcted area was smaller in the edaravone-treated group than in the control group in the embolization model of middle cerebral artery occlusion. These findings suggested that this chemical has inhibiting effects on infarction formation and reducing effects on the formation of infarction.

In rat infarction models, the functional deficits are recovered within about 2 weeks after the infarction. Therefore, a time-course study is important in order to evaluate the effects of medication or rehabilitation. In this study, we detected an enhanced effect of edaravone on functional recovery in infarcted rats.

Recently, 3-Methyl-1-phenyl-2-pyrazolin-5-one has been investigated in global brain ischemia and transient ischemic attacks. The combination therapy of this chemical with low temperatures has been reported. There has been a report that 3-Methyl-1-phenyl-2-pyrazolin-5-one was effective in neonatal cerebral ischemia and epilepsy. It has been studied in traumatic brain injury, spinal cord injury, neurodegenerative disease, and brain tumor. Thus, 3-Methyl-1-phenyl-2-pyrazolin-5-one is thought to have various effects on central nervous system disturbances.

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How to make 5-Hydroxymethylthiazole

5-Hydroxymethylthiazole is a kind of slightly yellow oil liquids, the Molecular Formula is C4H5NOS, Molecular weight is 115.15, and the CAS NO. is 38585-74-9. It is an important intermediate for Ritonavir, and a kind of anti-AIDS pharmaceuticals.

Since the discovery of 5-Hydroxymethylthiazole can be used for synthesis of second-generation anti-AIDS drugs ritonavir (Ritonavir), scientists have done many studies on the synthesis method of 5-Hydroxymethylthiazole. But how to prepare it, in this Article, I will introduce 3 new approaches：

Approach one

In a reaction flask IOOml 250ml of ethanol, 15g (0. Imol) 2_ chloro-5 - (hydroxymethyl) thiazole and 13. 5g (0. 20mol) zinc powder, the above mixture was heated to 50 C , then slowly add 150ml hydrochloric acid (2N), at a temperature of 70 C for 2 hours detected by TLC or HPLC, until the starting material disappeared, the reaction was stopped and the reaction solution was filtered, concentrated and neutralized with sodium hydroxide to PH of 10, and then extracted with ethyl acetate to give crude product, the final crude solvent was removed by distillation under reduced pressure, collecting 115 ~ 122 C (24mmHg) the distillate, 8. 5g 5 - (hydroxymethyl) thiazole. The determination of the purity% 99. 3% (HPLC), the yield was 74%.

Approach two

In a reaction flask IOOml 250ml of ethanol, 45g (0. 3mol) 2_ chloro-5 - (hydroxymethyl) thiazole and 33g (0. 5mol) zinc powder, and then added slowly 75ml hydrochloric acid (6N), the temperature of 60 C for 2 hours, by TLC or HPLC detection, until the starting material disappeared, the reaction was stopped and the reaction solution was filtered, concentrated and neutralized with sodium hydroxide to a PH of 10, and then extracted with ethyl acetate and to give the crude product, the final crude solvent was removed by distillation under reduced pressure, collecting 115 ~ 1220C (24mmHg) the distillate, 25g 5 - (hydroxymethyl) thiazole. The purity was determined 99. 5% (HPLC), the yield was 72%.

Approach three

2–Chloro-5-hydroxymethylthiazole hydrochloride(3.72 g 0.02 mole) was dissolved in methanol (30 mL) and charged into a Parr shaker. To this solution was charged sodium carbonate( 2.12 g 0.02 mole) and 10 palladium on carbon (0.9 g). The system was heated (60 C) under 50 psi (3.40 atm) of hydrogen gas and agitated for 18 hours. The reaction was monitored by TLC or GC and allowed to proceed for an additional 5 hours after completion. The reaction mixture was cooled and the contents filtered through a bed of diatomaceous earth. The filtrate was then concentrated under reduced pressure (38 C) and the residue was taken up in methyl t butyl ether (100 mL) and dried over sodium sulfate (10 g). The dried solution was filtered and concentrated under reduced pressure (38 C) to provide 5-hydroxymethylthiazole as a slightly colored oil Yield 

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Something important about Tetrakis(triphenylphosphine)palladium

Tetrakis(triphenylphosphine)palladium is one kind of yellow powder. The the IUPAC name of this chemical is palladium; triphenylphosphane. Besides, Tetrakis(triphenylphosphine)palladium belongs to straight chain compounds; Metal Compounds; blocks; pharmacetical; Catalysts-Ligands; Catalysts for Organic Synthesis; Classes of Metal Compounds; Homogeneous Catalysts; Metal Complexes; Pd (Palladium) Compounds; Synthetic Organic Chemistry; Transition Metal Compounds; Fine Chemical Catalysts; metal-phosphine complexes. 

In addition, Tetrakis(triphenylphosphine)palladium is insoluble in water. The compound is sensitive to air, but can be purified by washing with methanol to give the desired yellow powder.  The CAS NO is 14221-01-3. It is usually stored cold under argon.

The structure and properties: 

The four phosphorus atoms are at the corners of a tetrahedron surrounding the palladium(0) center. This structure is typical for four-coordinate 18e complexes. The corresponding complexes Ni(PPh3)4 and Pt(PPh3)4 are also well known. Such complexes reversibly dissociate PPh3 ligands in solution, so reactions attributed to Pd(PPh3)4 often in fact arise from Pd(PPh3)3 or even Pd(PPh3)2.

The mainly usages:

Tetrakis (triphenylphosphine) palladium is widely used as a catalyst for palladium-catalyzed coupling reactions. Prominent applications include the Heck reaction, Suzuki coupling, Stille coupling, Sonogashira coupling, and Negishi coupling. These processes begin with two successive ligand dissociations followed by the oxidative addition of an aryl halide to the Pd center:
Pd(PPh3)4 + ArBr → PdBr(Ar)(PPh3)2 + 2 PPh3

Material Safety Data Sheet (MSDS):

Ingestion: If victim is conscious and alert, give 2-4 cupfuls, milk or water. Do not give anything to eat, a person in a coma. Get medical attention immediately.
Inhalation: Get medical attention immediately. Immediately from the scene to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Skin: Get medical attention immediately. At least 15 minutes, but with plenty of soap and water to wash the skin, remove contaminated clothing and shoes.
Eyes: Flush with plenty of water for at least 15 minutes, rinse eyes, occasionally lifting the upper and lower eyelids. Get medical attention immediately.

Handling and storage:

Storage: Store Tetrakis(triphenylphosphine)palladium in a refrigerator (about 4 degree). Keep container tightly closed. Protected storage of light and air. Stored under argon. Store in a cool, dry place, away from incompatible substances.

Treatment: Wash thoroughly after handling Tetrakis(triphenylphosphine)palladium. Only in well-ventilated places. Minimize dust generation and accumulation. Avoid contact with eyes, skin and clothing. Avoid ingestion and inhalation. Stored protected from light. Stored protected from air. Under argon use and storage.


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