氨基硫脲

Thiosemicarbazide

HCID 2723789CAS 79-19-6

基本信息

标准SMILES
NNC(N)=S
InChIKey
BRWIZMBXBAOCCF-UHFFFAOYSA-N
分子式
CH5N3S
平均分子量
91.14 g/mol
单同位素质量
91.02041835

名称与标识

首选名称
Thiosemicarbazide
IUPAC
aminothiourea
中文名
氨基硫脲
英文名
Thiosemicarbazide
分子式
CH5N3S
分子量
91.14

名称与别名

Thiosemicarbazide79-19-6aminothioureaHydrazinecarbothioamideN-Aminothiourea1-AminothioureaIsothiosemicarbazide2-Thiosemicarbazide3-ThiosemicarbazideThiocarbamylhydrazineThiocarbamoylhydrazineSemicarbazide, thio-
展开更多名称
灭鼠特硫氨脲胺硫脲杀鼠特氨基硫脲硫半卡肼氨基硫尿硫代氨基脲硫代氯基硫脲N-氨基硫脲TSCTSZCHP3NSC 2213NSC 31792
Aminothio-ureaThiocarbamoyl hydrazide1-AMINO-2-THIOUREASemicarbazide, 3-thio-USAF EK-1275DTXSID9021346AI3-163196056O8W6ET

数据库标识

CAS
79-19-6
PubChem CID
2723789
DTXSID
DTXSID9021346
ChEMBL
CHEMBL256250
ChEBI
CHEBI:49929
UNII
6056O8W6ET
EC Number
201-184-7
Nikkaji
J2.410D

性质

结构计算性质

XLogP
-1.2
极性表面积
96.2 Ų
氢键供体
3
氢键受体
2
可旋转键
0
重原子
5

实验与物化性质

OdorOdorless
Color/Form · 2 条

White crystalline powder

Long needles from water

Solubility · 4 条

In water, 1./0X10+4 mg/L at 20 °C

Very soluble in water

Soluble in water or alcohol

Very soluble in ethanol

DecompositionWhen heated to decomposition it emits very toxic fumes of NOx and SOx.
Melting Point · 3 条

356 to 363 °F (EPA, 1998)

183 °C

183 °C

Vapor Pressure0.33 [mmHg]

物理化学性质

熔点
180 · 180-183 °C (dec.)(lit.)
沸点
208.6 · 208.6±23.0 °C(Predicted)
堆积密度
500 · 500-600kg/m3
密度
1.221 · 1.221 (estimate)
蒸气压
1.15 Pa · 1.15Pa at 25℃
折射率
1.58 · 1.5800 (estimate)

化学性质

白色结晶或白色结晶性粉末。 溶于水和乙醇。

安全与法规

GHS分类

GHS Classification · 6 条

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral];H412 (27.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P264, P270, P273, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 83 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

H402: Harmful to aquatic life [Hazardous to the aquatic environment, acute hazard];H412: Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

危害信息

Regulatory Information · 4 条

Chemical: Hydrazinecarbothioamide

Status: Active Update: 09-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17647;Status: Active Update: 13-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20705

Thiosemicarbazide: HSNO Approval: HSR004724 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsWhen heated to decomposition, very toxic fumes of sulfur oxides and nitrogen oxides are emitted. (EPA, 1998)
Health HazardsThis material is highly toxic by ingestion. May induce goiter and cause delayed toxic effects in blood and skin. May be mutagenic in human cells. (EPA, 1998)
Hazards Summary · 1 条

May cause irritation, goiter, bone marrow depression, hyperglycemia, CNS excitation, seizures, and pulmonary edema after ingestion; A GABA synthesis inhibitor in experimental animals; [HSDB] Causes convulsions in lethal-dose studies of guinea pigs, mice, and cats (oral, ocular, intravenous, and intraperitoneal routes); [RTECS] An irritant; [Alfa Aesar MSDS]

Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds;Isocyanates and Isothiocyanates

安全与防护

Fire Fighting · 1 条

(Non-Specific -- Poisonous, Solid, n.o.s.) Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. Move container from fire area if you can do so without risk.;(Non-Specific -- Poisonous, Solid, n.o.;s) Extinguish with any chemical, carbon dioxide, water spray, fog, or foam. (EPA, 1998)

First Aid · 1 条

Warning: Highly toxic by ingestion. May be mutagenic in human cells.;Signs and Symptoms of Thiosemicarbazide Exposure: Signs and symptoms of acute exposure to thiosemicarbazide may include eye and skin irritation, excessive salivation, vomiting, pulmonary edema, pleural effusions, central nervous system stimulation, and seizures.;Emergency Life-Support Procedures: Acute exposure to thiosemicarbazide may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination.;Inhalation Exposure:;1. Move victims to fresh air. Emergency personnel should avoid self-exposure to thiosemicarbazide.;2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support.;3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures.;4. Transport to a health care facility.;Dermal/Eye Exposure:;1. Remove victims from exposure. Emergency personnel should avoid self-exposure to thiosemicarbazide.;2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support.;3. Remove contaminated clothing and shoes as soon as possible.;4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes.;5. Wash exposed skin areas thoroughly with soap and water.;6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures.;7. Transport to a health care facility.;Ingestion Exposure:;1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support.;2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.;3. DO NOT induce vomiting.

Firefighting HazardsSpecial hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), sulphur oxides.
Fire Fighting Procedures · 2 条

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Storage ConditionsConditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place.
Cleanup Methods · 1 条

Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

毒理信息

Interactions · 5 条

The acute neurobehavioral toxicity of organochlorine pesticide, aldrin, has been studied at sublethal doses. A dose of 8.9 mg/kg (1/4 LD50) induced piloerection, tremors, convulsive excitement restlessness, augmented spontaneous motor activity and exploratory behavior in mice after 60 min, of i.p. administration indicating CNS stimulation. Blockade of specific neurotransmitter system by pretreatment with atropine (10 mg/kg), iproniazid (100 mg/kg) alpha-methyl-p-tyrosine (200 mg/kg), p-chlorophenylalanine (200 mg/kg) or thiosemicarbazide (5 mg/kg) significantly altered the neurotoxic symptoms induced by the pesticide indicating direct or indirect involvement of various neurotransmitter system in mediating CNS toxicity. Conditioned avoidance response in rats was not affected by the pesticide alone or in combination with either drug.

Female CD1 mice given the contraceptive steroids mestranol and norethynodrel (1:10) in the diet (0.0033%) for 4 months had a growth reduction of 20% when compared with mice fed a normal diet, and had lower convulsive thresholds when tested with the vitamin B6 antagonists 2,4-dimethyl-5-methyl-hydroxypyrimidine and thiosemicarbazide. In conditioned avoidance response (CAR) tests, mice fed the steroid-containing diets showed a decreased acquisition performance during all six sessions; however, mice fed the same diet supplemented with vitamin B6 (0.04%) performed as well during the last three sessions of the CAR tests as mice fed the normal diet.

Susceptibility to thiosemicarbazide was compared in 7 animal species together with the protective effect of vitamin B6 on the induction of convulsions. Susceptibility occurred generally with the phylogenetic development of the brain of vertebrates as well as invertebrates. Abnormal behavior analogous to running fits in rats and mice, which was thought to be a characteristic and activated form of locomotion, was also induced in every animal except the silkworm. Vitamin B6 arrested the induction of convulsions and abnormal behavior in guinea pigs and goldfish.

GABA-/inhibitory/ agents (thiosemicarbazide) markedly decreased the effect of morphine, hydrocodone, and the enkephaline analogs: Tyr-D-Ala-Gly-Phe-NH2 and Tyr-D-Ala-Gly-Phe (NO2) NH2 /in experimental animals/.

For more Interactions (Complete) data for 1-AMINO-2-THIOUREA (15 total), please visit the HSDB record page.

Ecotoxicity Values · 3 条

LC50; Species: Xenopus laevis /(African clawed frog)/ embryos; Concentration: 10,970 mg/L for 96 hr /Conditions of bioassay not specified in source examined/

EC50; Species: Xenopus laevis /(African clawed frog)/ embryos; Concentration: 25.5 mg/L for 96 hr; Effect: gross embryo malformation /Conditions of bioassay not specified in source examined/

LD50; Species: Wild bird oral 9100 ug/kg

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 16(SRC), determined from a structure estimation method(2), indicates that 1-amino-2-thiourea is expected to have very high mobility in soil(SRC). Volatilization of 1-amino-2-thiourea from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.6X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 1-Amino-2-thiourea is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.0087 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Utilizing the Japanese MITI test, 0% of the theoretical BOD was reached in 4 weeks indicating that biodegradation in soil is not an important environmental fate process(3).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 16(SRC), determined from a structure estimation method(2), indicates that 1-amino-2-thiourea is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.6X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). 1-Amino-2-thiourea may undergo hydrolysis in the environment due to functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(4), BCFs of 3.8-4.2 and <39 in carp (Cyprinus carpio)(5), suggest bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 0% of the theoretical BOD was reached in 4 weeks indicating that biodegradation in water is not an important environmental fate process(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-amino-2-thiourea, which has an estimated vapor pressure of 0.008 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-amino-2-thiourea is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 hours(SRC), calculated from its rate constant of 8.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase 1-amino-2-thiourea may be removed from the air by wet and dry deposition(SRC). 1-Amino-2-thiourea contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity Summary · 1 条

IDENTIFICATION AND USE: 1-Amino-2-thiourea is an odorless white crystalline powder or long needles from water. It is an intermediate for pesticides, especially herbicides, and pharmaceuticals; used in certain photographic and dye applications and used as a reagent for the detection of metals. HUMAN EXPOSURE AND TOXICITY: Thioureas are potential sensitizing accelerators and antioxidants used in the manufacture of rubber which may cause irritant contact dermatitis. ANIMAL STUDIES: Subcutaneous injections of thiosemicarbazide into postnatal mice caused convulsions in mice when treated on the day 7 or later but not on the days 1-5. The latent period of the 1st convulsion was 115 min in mice injected on the day 7. The convulsions were inhibited by pyridoxine-HCL, but not by pyridoxal phosphate. GABAergic antagonists (1-amino-2-thiourea) enhanced aggressive behavior and decreased the social behavior of mice. 1-amino-2-thiourea was noncarcinogenic in mice and rats. The agent was teratogenic in chick embryos when applied to the vascular area on the 3rd day of incubation at 0.5 to 1 mg it produced deformities of the wing and beak, but not harelip. ECOTOXICITY STUDIES: Exposure of Rana sylvatica tadpoles to 25 mg/L or more caused a curvature of digits, abnormal limb articulations, difficulty in swimming, and death. Wood frog (Rana sylvatica) tadpoles were exposed to 50 mg thiosemicarbazide (TSC)/L water for varying lengths of time and at different developmental stages. Short exposure periods (3 and 6 hr) resulted in no visible deformities. Exposure periods of 12 or more hr caused slight to severe abnormalities, with a direct relationship between length of exposure and degree of deformity. Tadpoles exposed to TSC from posthatching Days 24-30 were more seriously affected than were tadpoles exposed at an older age.

Ecotoxicity Excerpts · 2 条

/AQUATIC SPECIES/ The effects of exposure of Rana sylvatica tadpoles to varying concentrations (10-75 mg/L for 4 days) of thiosemicarbazide (TSC) was studied. Exposure to concentrations of 25 mg/L or more caused a curvature of digits, abnormal limb articulations, difficulty in swimming, and death. For all of these parameters, effects were dose dependent. Tadpoles exposed to 10 mg/L metamorphosed significantly slower than controls while those exposed to 50 mg/L metamorphosed significantly faster than controls. Rate of endochondral ossification in femurs and tibio-fibulas also was affected by TSC. These long bones ossified faster than in controls in both the 25- and 75-mg/L exposure groups. R. sylvatica tadpoles respond to TSC (a known osteolathyrogen) in a manner similar to that of other species. This response appears to be due in part to an acceleration of long bone ossification and speed of metamorphosis in high-concentration exposure groups. These responses are similar but not identical to those seen in Xenopus laevis, the only other amphibian studied to date.

/AQUATIC SPECIES/ Wood frog (Rana sylvatica) tadpoles were exposed to 50 mg thiosemicarbazide (TSC)/L water for varying lengths of time and at different developmental stages. Short exposure periods (3 and 6 hr) resulted in no visible deformities. Exposure periods of 12 or more hr caused slight to severe abnormalities, with a direct relationship between length of exposure and degree of deformity. Tadpoles exposed to TSC from posthatching Days 24-30 were more seriously affected than were tadpoles exposed at an older age.

法规信息

Regulatory Information · 4 条

Chemical: Hydrazinecarbothioamide

Status: Active Update: 09-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17647;Status: Active Update: 13-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20705

Thiosemicarbazide: HSNO Approval: HSR004724 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

RCRA Requirements · 1 条

P116; As stipulated in 40 CFR 261.33, when hydrazinecarbothioamide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

CERCLA Reportable Quantities · 2 条

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Thiosemicarbazide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

安全数据

F
8-9-23
wgk
3
tsca
TSCA listed
毒性
LD50 orally in adult Norway rats: 13 mg/kg, Dieke, Proc. Soc. Exp. Biol. Med. 70, 688 (1949)
RTECS号
VT4200000
包装类别
II

毒性防护

急性毒性口服- 大鼠 LD50: 9.16 毫克/ 公斤

包装储运 · 3 条

可燃性危险特性燃烧产生有毒硫氧化物和氮氧化物气体

储运特性库房通风低温干燥; 与食品原料分开储运

灭火剂干粉、泡沫、砂土

化学与工业

药理信息

Mechanism of ActionGlutamic acid decarboxylase activity in mouse brain homogenates was reduced after pretreatment with thiosemicarbazide.
MeSH Pharmacological Classification · 2 条

Substances that act in the brain stem or spinal cord to produce tonic or clonic convulsions, often by removing normal inhibitory tone. They were formerly used to stimulate respiration or as antidotes to barbiturate overdose. They are now most commonly used as experimental tools.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

用途与制造

Uses · 6 条

Used as a reagent for ketones and detection of metals, rodenticide, and chemical intermediate; Also used in photography; [HSDB] Effective for controlling bacterial leaf blight in rice: [CAMEO]

Not registered as a pesticide for use in the US; [CAMEO]

Photographic Processing [Category: Other]

Reagent for ketones and certain metals; photography; rodenticide.

CHEM INT FOR HERBICIDES (EG, TEBUTHIURON); REAGENT FOR DETECTION OF METALS (POSSIBLE USE).

Used as chemical intermediates.... are useful in forming 1,3,4-thiadiazoles, as a class of compounds having herbicidal activity. /Thiosemicarbazides/

U.S. Imports(1977) AT LEAST 4.99X10+6 G
U.S. Production(1977) AT LEAST 4.54X10+6 G
Methods of Manufacturing · 2 条

... Made from CS2 and hydrazine.

From potassium thiocyanate and hydrazine salts.

Formulations/PreparationsGrades: technical and pure.
General Manufacturing Information · 2 条

Hydrazinecarbothioamide: ACTIVE

Thiosemicarbazide is effective for control of bacterial leaf blight of rice when applied around rice plant roots.

应用领域 · 6 条

用途用于合成抗结核药氨硫脲和磺胺药物,用作农药中间体、橡胶助剂、合成树脂添加剂以及分析试剂等

用途氨基硫脲又名硫代氨基脲,是制备氨基甲酸酯类杀虫剂唑蚜威以及噻二唑类杀菌剂和杀鼠剂的中间体,也可用于合成抗结核药氨硫脲和磺胺药物、橡胶助剂和合成树脂添加剂等,还可用作铬的定量及醛酮鉴定的分析试剂。

用途氨基硫脲是重要的有机合成中间体,常用于合成2-取代肼基-4-取代基噻唑类抗菌素,如硝呋喃唑(Nifurthiazole)以及抗病毒药酞丁安(Ftibamzone)等。

用途用作铬的定量测定及醛酮鉴定的分析试剂;用作铜的络合剂

用途铜的络合剂。测定铬的沉淀剂。检定某些金属和糖、醛、酮的试剂。毒鼠药制备。本品为有机合成中间体,用于合成抗结核药氨硫脲和磺胺药物,以及杀鼠剂。还可用作铬的定量及醛酮鉴定的分析试剂。此外,本品也用作农药中间体、橡胶助剂和合成树脂添加剂等。

用途用作分析试剂

制备方法 · 2 条

生产方法氨基硫脲是以水合肼、硫氰酸铵为原料,以乙醛为催化剂制得。反应方程式见:2H2NNH2·H2O+H2SO4→(H2NNH2)2·H2SO4+2H2O(H2NNH2)2·H2SO4+2NH4SCN→2H2NNH2·HSCN+(NH4)2SO4先将一定量的水合肼放入三口瓶内,以水冷却,在搅拌下缓慢加入一定浓度的硫酸,保持温度在40℃以下,控制pH=4~5为终点即得硫酸肼。然后加入硫氰酸铵,搅拌,在30℃加入一定量乙醛(或丙酮),然后趁热将反应物移至烧杯中,在室温下放置4h,析出结晶,经过滤、水洗、干燥而得成品,收率80%以上。另外,也可以硫脲与水合肼为原料进行加热反应制得。

生产方法1.以硫脲与水合肼为原料进行加热反应制得。2.由水合肼与硫酸配制成硫酸肼,与硫氰酸铵反应生成硫氰酸肼,再与乙醛反应后经水解得到氨基硫脲。

试剂价格

A14630 · 2500g
氨基硫脲Thiosemicarbazide98% — 3321元
T0221 · 25G
氨基硫脲Thiosemicarbazide — 210元

供应商50 家

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北海克斯生化有限公司17362916295; 17362916295 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

相关反应

495 条

关联笔记

加载中…