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1,1'-azobisformamide | 123-77-3

中文名称
——
中文别名
——
英文名称
1,1'-azobisformamide
英文别名
AZODICARBONAMIDE;diazenedicarboxamide;azodicarboxamide;trans-diazenedicarboxylic acid diamide;trans-Diazendicarbonsaeure-diamid;(E)-carbamoyliminourea
1,1'-azobisformamide化学式
CAS
123-77-3
化学式
C2H4N4O2
mdl
——
分子量
116.079
InChiKey
XOZUGNYVDXMRKW-AATRIKPKSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    220-225 °C (dec.)(lit.)
  • 沸点:
    217.08°C (rough estimate)
  • 密度:
    1.65
  • 闪点:
    225 °C
  • 溶解度:
    水:20°C时可溶0.033g/L
  • LogP:
    -1.148 (est)
  • 物理描述:
    Azodicarbonamide appears as a yellow to orange powder. Insoluble in water and common solvents. Soluble in dimethyl sulfoxide. Nontoxic.
  • 颜色/状态:
    Orange-red crystals
  • 蒸汽压力:
    1.88X10-10 mm Hg @ 20 °C
  • 稳定性/保质期:

    Does not react with plasticizers and other components of plastics.

  • 分解:
    /Azoformamide/ shows a high rate of pressure rise on thermal decomposition. Energy of decomposition (in range 160-230 °C) measured as 1.36 kJ/g by /Differential Scanning Calorimeter/, and Tait24 was determined as 120 °C by adiabatic Dewar tests, with an apparent energy of activation of 131 kJ/mol.

计算性质

  • 辛醇/水分配系数(LogP):
    -1
  • 重原子数:
    8
  • 可旋转键数:
    0
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    111
  • 氢给体数:
    2
  • 氢受体数:
    2

ADMET

代谢
偶氮二甲酰胺很容易转化为双尿素,这是唯一识别的分解产物,而且系统暴露很可能主要是针对这种衍生物,而不是母体化合物。
Azodicarbonamide is readily converted to biurea, the only breakdown product identified, and it is likely that systemic exposure is principally to this derivative rather than to the parent compound.
来源:Hazardous Substances Data Bank (HSDB)
代谢
ADA迅速转化为双尿素,然后双尿素从所有组织中快速消除,大部分通过尿液排出。
... ADA is rapidly converted to biurea and that biurea is then eliminated rapidly from all tissues with the majority of the elimination via the urine.
来源:Hazardous Substances Data Bank (HSDB)
代谢
偶氮二甲酰胺可以很容易地转化为双尿素,这是唯一被识别的分解产物,而且系统暴露主要是这种衍生物,而不是母化合物。双尿素随后会迅速从所有组织中消除,大部分通过尿液排出(L1214, A336)。
Azodicarbonamide is readily converted to biurea, the only breakdown product identified, and it is likely that systemic exposure is principally to this derivative rather than to the parent compound. Biurea is then eliminated rapidly from all tissues with the majority of the elimination via the urine (L1214, A336).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 毒性总结
鉴定:偶氮二甲酰胺是一种合成化学品,在常温下以黄色橙色结晶固体形式存在。它不易溶于。人类接触:关于偶氮二甲酰胺在人类中诱发哮喘和皮肤过敏的研究已经取得了进展。有证据表明,偶氮二甲酰胺可以在人体中诱发哮喘,这一发现来自对有症状个体的支气管激发研究和在生产或使用该化学品的场所进行的员工健康评估。由于这种化学物质是人类哮喘的诱因,且目前尚不清楚诱发非敏感个体哮喘或激发敏感个体反应所需的浓度,因此可以认为,在目前的职业接触条件下,对人类健康存在风险。由于缺乏数据,无法评估普通公众接触该化学品的情况。动物研究:关于偶氮二甲酰胺的毒代动力学数据有限,但该化学品在大鼠和小鼠中通过吸入和口服途径似乎能很好地被吸收。大量的物质从胃肠道未被吸收,并通过粪便排出。该化合物很容易转化为双尿素甲酰胺),这是唯一确定的分解产物,因此系统暴露主要是这种衍生物而不是母体化合物。这种化合物和甲酰胺的消除是迅速的,主要通过尿液排出,甲酰胺的系统保留非常少。偶氮二甲酰胺的急性毒性较低,在实验动物中不引起皮肤、眼睛或呼吸道刺激。一项进行得不好的皮肤致敏研究的结果是阴性,而且在一次研究中,豚鼠没有出现哮喘样反应。反复口服暴露导致多种动物出现肾小管内出现管型结晶沉积的肾盂肾炎。诱导这些效应所需的剂量平很高。该化合物在细菌系统中被发现是一种致突变剂,但没有证据表明这种效应会在活体中表达。偶氮二甲酰胺的致癌性和生殖毒性尚未详细研究,但在早期使用分解产物甲酰胺对动物进行处理的研究中,没有观察到肿瘤发生或抗生育效应。尚未研究发育毒性。尚未报告鱼类和蚤的无观察效应浓度(NOECs)。
IDENTIFICATION: Azodicarbonamide is a synthetic chemical that exists at ambient temperatures as a yellow orange crystalline soild. It is poorly soluble in water. HUMAN EXPOSURE: Studies in humans have concentrated soley on the ability of this chemical to induce asthma and skin sensitization. Evidence that azodicarbonamide can induce asthma in humans has found from bronchial challenge studies with symptomatic individuals and from health evaluations of employees at workplaces where this cgemical is manufactured or used. On the basis that this chemical is a human asthmagen and the concentrations required to induce asthma in a non-sensitive individual or to provoke a response in a sensitive individual is unknown, it is concluded that there is a risk to human health under present occupational exposure conditions. Exposure of the general public to this chemical could notbe evaluated because of the lack of data. ANIMAL STUDIES: Toxicokinetic data on azodicarbonamide are limited, but the chemical appears to be well absorbed by the inhalation and oral routes of in rodents. Substantial quantities of the substance remain unabsorbed from the gastrointestinal tract and are passed out in the feces. The compound is readily converted to biurea (hydrazocarbonamide), the only breakdown product identified, and it is likely that systemic exposure is principally to this derivative rather than to the parent compound. Elimination of this compound and hydrazocarbonamide is rapid, occurring predominantly via the urine, and there is very little systemic retention of hydrazocarbonamide. Azodicarbonamide is of low acute toxicity and does not cause skin, eye or respiratory tract irritation in experimental animals. Results from a poorly conducted skin sensitization study were negative, and there was no evidence of an asthmatic type response in guinea pigs in one study. Repeated oral exposures resulted in the appearance of pyelonephritis with casts and crystalline deposits in renal tubuli in several species. The dose levels required to induce these effects were high. This compound was found to be a mutagen in bacterial systems, there was no evidence this effect would be expressed in vivo. The carcinogenicity and reproductive toxicity of azodicarboxamide have not been examined in detail, but no tumorigenic or antifertility effects were observed in early studies in which animals were treated wit the breakdown product hydrazocarbonamide. Developmental toxicity has not been studied. No observed effect concentrations (NOECs) for fish and the water flea have been reported.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
偶氮二甲酰胺可阻止人CD4+ T淋巴细胞的细胞周期进入G1期,抑制其母细胞转化,下调其膜上CD25和CD69的表达,并减少细胞因子基因的转录(A337)。
Azodicarbonamide prevents the progression of human CD4+ T lymphocytes into the G1 phase of the cell cycle, inhibits their blastogenesis, down-regulates their membrane expression of CD25 and CD69, and decreases their transcription of cytokine genes (A337).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 致癌物分类
对人类不具有致癌性(未被国际癌症研究机构IARC列名)。
No indication of carcinogenicity to humans (not listed by IARC).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 健康影响
中毒可能导致人的肺部过敏和皮炎(L1214)。
Poisoning can cause pulmonary sensitization and dermatitis in people (L1214).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 暴露途径
该物质可以通过吸入其气溶胶被吸收进入人体。
The substance can be absorbed into the body by inhalation of its aerosol.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
吸收、分配和排泄
30%的剂量通过灌胃给F344大鼠,在给药后72小时内被发现被吸收。经吸入后,1,1-偶氮双甲酰胺在生理条件下很容易转化为双尿素,双尿素是排泄物中唯一含14C标记的化合物。主要通过尿液排出。
30% of the dose given by gavage to F344 rats was found to be absorbed in 72 hr after administration. Upon inhalation, /1,1-azobisformamide/ is readily converted into biurea under physiological conditions, and biurea was the only 14C-labeled compound present in excreta. Excretion occurs predominantly via the urine.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
偶氮二甲酰胺的吸收已经在单次吸入暴露长达6小时(剂量的34%)和单次口服给药(剂量的10-33%)给大鼠的放射标记偶氮二甲酰胺后得到证实。相比之下,大约90%的单次气管内滴注剂量显然被吸收。吸入和气管内滴注偶氮二甲酰胺之间的吸收差异可能与大量吸入的偶氮二甲酰胺没有到达下呼吸道有关。在大鼠仅鼻子暴露于25 mg/立方米干气溶胶(平均空气动力直径为3.4微米)6小时后半小时,计算出的总摄入量的78%位于消化道。通过吸入和口服途径暴露后,大量的物质仍然未被消化道吸收,并通过粪便排出。...吸收的偶氮二甲酰胺/双尿素的消除是迅速的,主要发生在尿液中,双尿素的系统性保留非常少。
Absorption of azodicarbonamide has been demonstrated following both a single inhalation exposure of up to 6 hr (34% of dose) and a single oral administration (10-33% of dose) of radiolabelled azodicarbonamide to rats. In contrast, approximately 90% of a single intratracheally instilled dose was apparently absorbed. The difference in absorption between inhaled and intratracheally instilled azodicarbonamide could be related to the fact that much of the inhaled azodicarbonamide did not reach the lower respiratory tract. Half an hour after a 6-hr nose-only exposure of rats to 25 mg/cu m of a dry aerosol (average mass aerodynamic diameter 3.4 um), 78% of the calculated total intake was located in the gastrointestinal tract. Following exposure by both inhalation and oral routes, substantial quantities of the substance remain unabsorbed from the gastrointestinal tract and are passed out in the feces. ...Elimination of absorbed azodicarbonamide/biurea is rapid, occurring predominantly via the urine, and there is very little systemic retention of biurea.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险等级:
    4.1
  • 危险品标志:
    Xn
  • 安全说明:
    S22,S24,S37
  • 危险类别码:
    R44,R42
  • WGK Germany:
    1
  • 海关编码:
    2924199090
  • 危险品运输编号:
    UN 3242 4.1/PG 2
  • 危险类别:
    4.1
  • RTECS号:
    LQ1040000
  • 包装等级:
    II

SDS

SDS:b9a828eef9ff324c230c60032caeab6a
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制备方法与用途

鉴别试验

取试样35mg,溶于1000ml中。该溶液的紫外线最大吸收作用在波长245nm处。

含量分析

准确称取约225mg(在50℃下真空干燥2h后)的试样,放入一250ml具玻塞量瓶中。加入二甲基亚砜约23ml,洗下可能附于壁上的试样,加塞,在塞子周围盛上2ml该溶剂。偶尔转动一下,至试样完全溶解。去掉瓶塞,使剩余的溶剂连同可能溶解的试样流入烧瓶。用15ml将5.0g碘化钾洗入烧瓶,随后立即吸取0.5mol/L盐酸10ml移入烧瓶,迅速塞盖。摇动瓶子至碘化钾完全溶解,然后在避光条件下静置20~25min,用0.1mol/L硫酸滴定至所析出的的黄色消失,在15min内如重新出现黄色,则再用硫酸滴定至无色。另取25ml二甲基亚砜、5.0g碘化钾、15ml和5mL0.5mol/L盐酸进行空白试验。每毫升0.1mol/L硫酸相当于偶氮甲酰胺(C₂H₄N₄O₂)5.804mg。

毒性

可安全用于食品(FDA,§172.806,2000)。 ADI 0~45(FAO/WHO,2001)。

使用限量
  • GB 2760-1996:小麦粉0.045g/kg。
  • FAO/WHO,1965:45mg/kg小麦粉。
  • 日本,1999:谷物粉、面包面团,45mg/kg。
化学性质

黄色粉末。无臭。溶于碱和二甲基亚砜,不溶于醇、汽油、苯、吡啶

用途
  • 小麦粉处理剂;焙烤食品快速发酵剂。
  • 在低用量下可完成对小麦粉的安全快速氧化,以改善面团的物理性能和高筋面团所需的组织结构。
  • 面粉处理剂,我国规定可用于小麦粉中,最大使用量为0.2g/kg(以成品计)。
  • 还可用于合成染料、塑料稳定剂等。
生产方法

尿素溶于2%的溶液,搅拌,并加入硫酸,使pH值达到1~2,然后加热使pH值为2~5,再缓缓加入硫酸,保持pH值2~5,反应数小时后取样测定终点;反应结束后,过滤去除硫酸母液,并用热洗涤得联二。将联二溶于,加入溴化钠,通入气,在30~50℃反应;反应混合物用温洗至中性,再离心甩干、干燥得成品。

原料消耗定额:(40%)1160kg/t、尿素(含氮量≥46%)1330kg/t、液800kg/t、烧碱(30%)2000kg/t、硫酸(98%)1140kg/t。

类别
  • 易燃固体
  • 毒性分级:低毒
  • 急性毒性:口服-大鼠 LD50; >6400 毫克/公斤
  • 爆炸物危险特性:低过
  • 敏剂
  • 可燃性危险特性:易燃;燃烧产生有毒氮氧化物烟雾
  • 储运特性:通风低温干燥
灭火剂

干粉、泡沫、沙土、二氧化碳、雾状

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    POGREBNOJ, A. M.;SOKOLOV, V. N.;KOLESNIKOV, A. A., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 32,(1989) N1, S. 86-91
    摘要:
    DOI:
  • 作为产物:
    描述:
    联二脲 以93%的产率得到
    参考文献:
    名称:
    DRAGUTAN, VALERIAN;DRAGUTAN, ILEANA;VINATORU, MIRCEA;MEDVEDIC, CONSTANTIN+
    摘要:
    DOI:
  • 作为试剂:
    描述:
    邻碘溴苯4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide二异丙胺 作用下, 以 1,1'-azobisformamide 为溶剂, 生成 4-(2-bromophenylethynyl)anisole
    参考文献:
    名称:
    Emission from Regioisomeric Bis(phenylethynyl)benzenes during Pulse Radiolysis
    摘要:
    Emission from charge recombination between radical cations and anions of a series of regioisomeric 1,4-, 1,3-, and 1,2-bis(phenylethynyl)benzenes (bPEBs) substituted by various electron donor and/or acceptor groups was measured during pulse radiolysis in benzene (Bz). The formation of bPEB in the excited singlet state ((1)bPEB*) can be attributed to the charge recombination between bPEB(center dot+) and bPEB(center dot-), which are initially generated from the radiolytic reaction. This mechanism is reasonably explained by the relationship between the annihilation enthalpy change (-Delta H degrees) for the charge recombination of bPEB(center dot+) and bPEB(center dot-) and excitation energy of (1)bPEB*. Since the degree of the pi-conjugation in the S-1 state and HOMO-LUMO levels of bPEB change with the substitution pattern of phenylacetylene groups on the central benzene ring and the various kinds of donor and/or acceptor group, the fine-tuning of the emission color and intensity of bPEB can be easily carried out during pulse radiolysis in Bz. For donor-acceptor-substituted bPEB, it was found that the difference in the charge transfer conjugated pathways between donor and acceptor substituents (linear-, cross-, and "bent"-conjugated pathways) strongly influenced the HOMO-LUMO energy gap.
    DOI:
    10.1021/jo900494j
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文献信息

  • Method for producing sulfonyl semicarbazides
    申请人:Armstrong Cork Company
    公开号:US03933909A1
    公开(公告)日:1976-01-20
    A new synthetic route to sulfonyl semicarbazides wherein an azobisformamide is reacted with a free sulfinic acid.
    一种新的合成磺酰腙的方法,其中偶氮二甲酰胺与自由亚磺酸反应。
  • 2,N-6-disubstituted adenosines and their antihypertensive methods of use
    申请人:Glaxo Group Limited
    公开号:US05032583A1
    公开(公告)日:1991-07-16
    Compounds of formula (I) ##STR1## wherein X represents a hydrogen or chlorine atom, or a methyl group; and R represents a cycloalkyl or cycloalkenyl ring containing 5 to 8 carbon atoms, which ring is substituted by a hydroxy group, and is optionally substituted by a C.sub.1-6 alkyl group and salts and solvates thereof. The new compounds have been found to exhibit activities such as an anti-lipolytic action. Processes for preparing the compounds of formula (I) and compositions containing them are also described.
    公式(I)的化合物 其中X代表氢原子、原子或甲基基团;R代表含有5至8个碳原子的环状烷基或环状烯基环,该环被羟基取代,并且可以被C.sub.1-6烷基取代,以及其盐和溶剂化物。已发现这些新化合物具有抗脂解作用等活性。本文还描述了制备公式(I)化合物的方法和含有它们的组合物。
  • Divergent Synthesis of Trifluoromethyl-Substituted 1,2-Dihydroquinoxalines and Diimines by Cascade Reactions of CF<sub>3</sub>–Imidoyl Sulfoxonium Ylides with Azo Compounds
    作者:Guangming Wei、Dongling Zheng、Chen Li、Zhengkai Chen、Xiao-Feng Wu
    DOI:10.1021/acs.orglett.3c02718
    日期:2023.9.29
    A base-mediated cascade reaction of CF3-imidoyl sulfoxonium ylides and azo compounds has been achieved, allowing for facile access to trifluoromethyl-substituted 1,2-dihydroquinoxalines and diimines in moderate to excellent yields. Noteworthy is that the unusual N–N bond cleavage and rearrangement of azo compounds are involved in the transformations.
    已经实现了CF 3 -亚酰亚磺鎓叶立德和偶氮化合物的碱介导级联反应,可以以中等至优异的产率轻松获得三甲基取代的1,2-二氢喹喔啉和二亚胺。值得注意的是,偶氮化合物不寻常的 N-N 键断裂和重排参与了转变。
  • Formamoylation of some azo compounds and the characterization of reaction products
    作者:Richard M. Fantazier、John E. Herweh
    DOI:10.1021/jo00954a036
    日期:1973.7
  • 1, 2-dicarbamyl-1, 2, 3, 6-tetrahydropyridazines and their preparation
    申请人:STERLING DRUG INC
    公开号:US02813867A1
    公开(公告)日:1957-11-19
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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同类化合物

(乙腈)二氯镍(II) (R)-(-)-α-甲基组胺二氢溴化物 (N-(2-甲基丙-2-烯-1-基)乙烷-1,2-二胺) (4-(苄氧基)-2-(哌啶-1-基)吡啶咪丁-5-基)硼酸 (11-巯基十一烷基)-,,-三甲基溴化铵 鼠立死 鹿花菌素 鲸蜡醇硫酸酯DEA盐 鲸蜡硬脂基二甲基氯化铵 鲸蜡基胺氢氟酸盐 鲸蜡基二甲胺盐酸盐 高苯丙氨醇 高箱鲀毒素 高氯酸5-(二甲氨基)-1-({(E)-[4-(二甲氨基)苯基]甲亚基}氨基)-2-甲基吡啶正离子 高氯酸2-氯-1-({(E)-[4-(二甲氨基)苯基]甲亚基}氨基)-6-甲基吡啶正离子 高氯酸2-(丙烯酰基氧基)-N,N,N-三甲基乙铵 马诺地尔 马来酸氢十八烷酯 马来酸噻吗洛尔EP杂质C 马来酸噻吗洛尔 马来酸倍他司汀 顺式环己烷-1,3-二胺盐酸盐 顺式氯化锆二乙腈 顺式吡咯烷-3,4-二醇盐酸盐 顺式双(3-甲氧基丙腈)二氯铂(II) 顺式3,4-二氟吡咯烷盐酸盐 顺式1-甲基环丙烷1,2-二腈 顺式-二氯-反式-二乙酸-氨-环己胺合铂 顺式-二抗坏血酸(外消旋-1,2-二氨基环己烷)铂(II)水合物 顺式-N,2-二甲基环己胺 顺式-4-甲氧基-环己胺盐酸盐 顺式-4-环己烯-1.2-二胺 顺式-4-氨基-2,2,2-三氟乙酸环己酯 顺式-3-氨基环丁烷甲腈盐酸盐 顺式-2-羟基甲基-1-甲基-1-环己胺 顺式-2-甲基环己胺 顺式-2-(苯基氨基)环己醇 顺式-2-(苯基氨基)环己醇 顺式-2-(氨基甲基)-1-苯基环丙烷羧酸盐酸盐 顺式-1,3-二氨基环戊烷 顺式-1,2-环戊烷二胺二盐酸盐 顺式-1,2-环戊烷二胺 顺式-1,2-环丁腈 顺式-1,2-双氨甲基环己烷 顺式--N,N'-二甲基-1,2-环己二胺 顺式-(R,S)-1,2-二氨基环己烷铂硫酸盐 顺式-(2-氨基-环戊基)-甲醇 顺-2-戊烯腈 顺-1,3-环己烷二胺 顺-1,3-双(氨甲基)环己烷