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Cas Database

58-08-2

58-08-2

Identification

  • Product Name:Caffeine

  • CAS Number: 58-08-2

  • EINECS:200-362-1

  • Molecular Weight:194.193

  • Molecular Formula: C8H10N4O2

  • HS Code:29393000

  • Mol File:58-08-2.mol

Synonyms:1H-Purine-2,6-dione,3,7-dihydro-1,3,7-trimethyl-;1,3,7-Trimethyl-2,6-dioxopurine;1,3,7-Trimethylxanthine;3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione;7-Methyltheophylline;Alert-Pep;Asia migrine;DHCplus;Durvitan;Guaranine;Koffein;Mateina;Methyltheobromine;Midron extra;Miudol;Phensal;Refresh'n;SK 65 Compound;Shape Plus;StayAlert;Theine;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn, ToxicT

  • Hazard Codes:Xn,T,F

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Refer for medical attention . SYMPTOMS: Symptoms of exposure to this compound may include central nervous system stimulation, less drowsiness, less fatigue, more rapid and clearer flow of thought, decreased reaction time, affects on muscular coordination, accurate timing and arithmetic skills, nervousness, restlessness, insomnia, tremors and hyperesthesia. At higher doses, symptoms include focal and generalized convulsions, Cheyne-Stokes respiration, apnea of preterm infants, vomiting, nausea, effects on circulatory system, small decreases in heart rate, tachycardia, arrhythmias, premature ventricular contractions and vasodilation. Overdosage may cause death, emesis, convulsions, excitement, mild delirium, sensory disturbances such as ringing in the ears and flashes of light, tense and tremulous muscles, extrasystoles and quickened respiration. Continued excessive use may lead to digestive disturbances, constipation, palpitations, shortness of breath and depressed mental states. Other symptoms may include pulmonary edema, myocardial infarction, ventricular fibrillation, stomach cramps, chills, cerebral edema and hypokalemia. It may also cause rapid pulse, hallucinations, photophobia, gastroenteric distress and diuresis. Anxiety and irritability may occur. Gastric irritation, headache, fever, agitation, hyperventilation and respiratory failure may also occur. Dizziness has been reported. It may also cause irritation of the skin, eyes, mucous membranes and respiratory tract. ACUTE/CHRONIC HAZARDS: This compound is harmful by ingestion, inhalation or skin absorption. It is an irritant of the skin, eyes, mucous membranes and respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. Emergency and supportive measures: Maintain an open airway and assist ventilation if necessary. Treat seizures and hypotension if they occur. Extreme anxiety or agitation may respond to benzodiazepines such as IV lorazepam. Hypokalemia usually resolves without treatment but in severe poisonings may need treatment as it can contribute to life-threatening arrhythmias. Monitor ECG and vital signs for at least 6 hours after ingestion.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, powder. Flash point data for this chemical are not available; however, it is probably combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from food and feedstuffs. Well closed.Separated from food and feedstuffs. Well closed.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Relevant articles and documentsAll total 49 Articles be found

SERS multiplexing of methylxanthine drug isomersviahost-guest size matching and machine learning

Chio, Weng-I Katherine,Dinish, U. S.,Jones, Tabitha,Lee, Tung-Chun,Liu, Jia,Olivo, Malini,Parkin, Ivan P.,Perumal, Jayakumar

supporting information, p. 12624 - 12632 (2021/10/06)

Multiplexed detection and quantification of structurally similar drug molecules, methylxanthine MeX, incl. theobromine TBR, theophylline TPH and caffeine CAF, have been demonstratedviasolution-based surface-enhanced Raman spectroscopy (SERS), achieving highly reproducible SERS signals with detection limits down to ~50 nM for TBR and TPH, and ~1 μM for CAF. Our SERS substrates are formed by aqueous self-assembly of gold nanoparticles (Au NPs) and supramolecular host molecules, cucurbit[n]urils (CBn,n= 7, 8). We demonstrate that the binding constants can be significantly increased using a host-guest size matching approach, which enables effective enrichment of analyte molecules in close proximity to the plasmonic hotspots. The dynamic range and the robustness of the sensing scheme can be extended using machine learning algorithms, which shows promise for potential applications in therapeutic drug monitoring, food processing, forensics and veterinary science.

Method for synthesizing caffeine

-

, (2021/01/04)

The invention discloses a method for synthesizing caffeine, and relates to the technical field of preparation of heterocyclic compounds containing purine ring systems. The preparation method comprisesthe following steps: mixing cyanoacetic acid and acetic anhydride at 30-80 DEG C for reaction, adding a solvent and dimethylurea, cooling to room temperature after reflux reaction is finished, filtering, concentrating filtrate, combining solids to obtain dimethylacetamide, adding liquid caustic soda to adjust the pH to 8-11, and reacting at 80-100 DEG C to generate dimethyl 4AU; the method comprises the following steps: completely dissolving dimethyl 4AU in formic acid, adding sodium nitrite, reacting at room temperature, adding a catalyst, keeping the temperature at 30-70 DEG C, recovering the catalyst after the reaction is finished, and concentrating mother liquor to recover formic acid, thereby obtaining dimethyl FAU; adding water and liquid caustic soda into dimethyl FAU, and carryingout a ring-closure reaction to obtain theophylline sodium salt; the theophylline sodium salt is subjected to methylation reaction and refining to obtain caffeine. The method has the advantages of accessible raw materials, mild and controllable reaction conditions, fewer steps, high yield and greatly higher product quality, is simple to operate, and can easily implement industrial production.

Green synthesis of caffeine based on methylating reagent dimethyl carbonate and environmental friendly separating method

Yang, Shu-Zhen,Dong, Zhi-Qiang,Yin, Cheng-Cheng,Yue, Hui-Juan,Gao, Wei-Wei,Yang, Feng-Ke

, p. 1715 - 1720 (2020/03/27)

In this paper, a green process for the synthesis and separation of caffeine was reported. Theophylline sodium is used as the raw material, diazabicyclo[5.4.0]undec-7-ene as the catalyst, and Turkey red oil as the solvent, particularly, dimethyl carbonate was adopted in place of high toxic dimethyl sulfate to form a mixture of caffeine and by-product sodium bicarbonate. After converting sodium bicarbonate to sodium carbonate, the solubility difference between caffeine and sodium carbonate at 40°C was for the first time utilized to achieve the purpose of separating caffeine with an excellent yield of 98.4% and a purity of greater than 99.0%. Furthermore, both the reaction mother liquor and separation mother liquor can be recycled and reused during the reaction and separation processes, respectively, with little caffeine loss. No industrial waste was discharged in the process of the improved synthesis and separation, which is therefore environmental friendly.

Room-temperature palladium-catalyzed direct 2-alkenylation of azole derivatives with alkenyl bromides

Yao, Yun-Xin,Fang, Dong-Mei,Gao, Feng,Liang, Xiao-Xia

supporting information, p. 68 - 71 (2018/12/05)

Pd-catalyzed direct C2-alkenylation of azole derivatives proceeds efficiently under mild conditions, and the reaction of substituted benzoxazoles, oxazole and benzothiazole occurred even at room temperature. The substrate scope of the reaction was turned out to include mono-, di- and trisubstituted alkenyl bromides. To validate the scalability of this method, 5-Methyl-2-(prop-1-en-2-yl)benzoxazole (3c) was prepared on one-gram scale at room temperature.

Dehydroxymethylation of alcohols enabled by cerium photocatalysis

Zhang, Kaining,Chang, Liang,An, Qing,Wang, Xin,Zuo, Zhiwei

supporting information, p. 10556 - 10564 (2019/08/20)

Dehydroxymethylation, the direct conversion of alcohol feedstocks as alkyl synthons containing one less carbon atom, is an unconventional and underexplored strategy to exploit the ubiquity and robustness of alcohol materials. Under mild and redox-neutral reaction conditions, utilizing inexpensive cerium catalyst, the photocatalytic dehydroxymethylation platform has been furnished. Enabled by ligand-to-metal charge transfer catalysis, an alcohol functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional alkyl nucleophiles for radical-mediated 1,4-conjugate additions with Michael acceptors. A broad range of alcohols, from simple ethanol to complex nucleosides and steroids, have been successfully applied to this fragment coupling transformation. Furthermore, the modularity of this catalytic system has been demonstrated in diversified radical-mediated transformations including hydrogenation, amination, alkenylation, and oxidation.

Process route upstream and downstream products

Process route

caffeine-oxalic acid
114303-55-8

caffeine-oxalic acid

magnesium stearate
557-04-0

magnesium stearate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

magnesium(II) oxalate
547-66-0,879683-44-0

magnesium(II) oxalate

stearic acid
57-11-4

stearic acid

Conditions
Conditions Yield
In water; at 20 ℃;
Methyl formate
107-31-3

Methyl formate

1,3-Dimethylxanthine potassium salt
57533-87-6

1,3-Dimethylxanthine potassium salt

theophylline
58-55-9,75448-53-2

theophylline

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
Conditions Yield
In methanol;
97.5%
theophylline
58-55-9,75448-53-2

theophylline

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
Conditions Yield
With sodium hydroxide; dimethyl sulfate;
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

caffeic acid
331-39-5,501-16-6

caffeic acid

Conditions
Conditions Yield
1-methylxanthine
6136-37-4

1-methylxanthine

dimethyl sulfate
77-78-1

dimethyl sulfate

theophylline
58-55-9,75448-53-2

theophylline

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
Conditions Yield
1-methylxanthine
6136-37-4

1-methylxanthine

methyl iodide
74-88-4

methyl iodide

theophylline
58-55-9,75448-53-2

theophylline

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
Conditions Yield
methanol
67-56-1

methanol

1,3-Dimethylxanthine potassium salt
57533-87-6

1,3-Dimethylxanthine potassium salt

Methyl formate
107-31-3

Methyl formate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
Conditions Yield
With carbon monoxide; at 140 ℃; for 20h; under 37503 Torr;
97%
caffeine-oxalic acid
114303-55-8

caffeine-oxalic acid

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
Conditions Yield
In water; at 20 ℃; for 168h;
3,4,5,7-Tetrahydro-1,3,7-trimethyl-10-syn-phenyl-11-anti-(trans-2-phenylethenyl)-4,5-ethano-1H-purin-2,6-dion
79246-59-6

3,4,5,7-Tetrahydro-1,3,7-trimethyl-10-syn-phenyl-11-anti-(trans-2-phenylethenyl)-4,5-ethano-1H-purin-2,6-dion

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

trans,trans-1,4-Diphenyl-1,3-butadiene
886-65-7,538-81-8

trans,trans-1,4-Diphenyl-1,3-butadiene

Conditions
Conditions Yield
In acetonitrile; at 20 ℃; Irradiation; in dependence on temperature, solvent;
3,4,5,7-Tetrahydro-1,3,7-trimethyl-11-syn-phenyl-10-anti-(trans-2-phenylethenyl)-4,5-ethano-1H-purin-2,6-dion
79246-60-9

3,4,5,7-Tetrahydro-1,3,7-trimethyl-11-syn-phenyl-10-anti-(trans-2-phenylethenyl)-4,5-ethano-1H-purin-2,6-dion

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2,138455-22-8,95789-13-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

trans,trans-1,4-Diphenyl-1,3-butadiene
886-65-7,538-81-8

trans,trans-1,4-Diphenyl-1,3-butadiene

Conditions
Conditions Yield
In acetonitrile; at 20 ℃; further reagent: 2-methyltetrahydrofuran, 83 K;

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