97-18-7硫双二氯酚,97%

CAS号： 97-18-7

分子式： C12H6Cl4O2S 分子量： 356.04

• 硫氯酚

  英文名：bithionol

  CAS：	97-18-7	精确质量：	353.88400
  分子式：	C12H6Cl4O2S	LogP：	5.86260
  分子量：	356.05200	PSA：	65.76000

97-18-7硫双二氯酚,97%化合物描述

Bithionol is an anthelmintic used to treat Anoplocephala perfoliata (tapeworms) in horses and Fasciola hepatica (liver flukes).
Bithionol has antibacterial and anthelmintic properties along with algaecide activity. It was formerly used in soaps and cosmetics until the FDA banned it for its photosensitizing effects. The compound has been known to cause photocontact sensitization.
Bithionol has been shown to be a potent inhibitor of soluble adenylyl cyclase (sAC), an intracellular enzyme important in the catalysis of ATP to cAMP. Soluble adenylyl cyclase is uniquely activated by bicarbonate. The cAMP formed by this enzyme is associated with capacitation of sperm, eye pressure regulation, acid-base regulation, and astrocyte/neuron communication.
Based on its relationship to the organochlorine, hexachlorophene, which has been shown to be a successful, but isomer-specific inhibitor of soluble adenylyl cyclase, bithionol was chosen to study potential inhibitors of the sAC enzyme. These two organochlorine compounds have similar chemical structures. Bithionol has two aromatic rings with a sulfur atom bonded between them and multiple chlorine ions and hydroxyl groups coming off of the phenyl groups. These functional groups are capable of hydrophobic, ionic, and polar interactions.
These intermolecular interactions are capable of binding bithionol to the bicarbonate binding site of soluble adenylyl cyclase efficiently enough to cause a sort of competitive inhibition with the usual bicarbonate substrate. The side chain of Arginine 176 within the bicarbonate binding site of the sAC protein interacts significantly with the aromatic ring of the bithionol molecule. This allosteric, conformational change interferes with the ability of the active site of sAC to adequately bind ATP to convert it into cAMP. The Arginine 176 usually interacts with the ATP and other catalytic ions at the active site, so when it turns from its normal position to interact with the bithionol inhibitor, it no longer functions in keeping the ATP bound to the active site.
In another form of inhibition, bithionol is a much larger molecule than simple sodium bicarbonate, so it is large enough to reach through a small channel in the sAC compound and physically interfere with the ability of ATP to fit into and thus bind to the active site to be converted to cAMP.
This inhibition of the sAC enzyme by bithionol at the bicarbonate binding site is demonstrated through a mixed-inhibition graph, where higher concentrations of bithionol have a lower Vmax and a larger Km. This translates to a decreased rate of reaction and a decreased affinity between substrates when bithionol is in higher concentrations.
Unfortunately, in order for bithionol to potently inhibit the soluble adenylyl cyclase enzyme, it requires concentrations that are cytotoxic in vivo. Thus, it cannot be used as the therapeutic drug needed to inhibit soluble adenylyl cyclase and therefore decrease the accumulation of cAMP within the cell. However, it does shed some light on the search for a compound that will eventually be able to target the bicarbonate binding site of the soluble adenylyl cyclase enzyme. Bithionol is the first known sAC inhibitor to act through the bicarbonate binding site via a mostly allosteric mechanism.

97-18-7硫双二氯酚,97%基本信息

• 中文名称：

  硫氯酚

• 中文别名：

  双(2-羟基-3,5-二氯苯)硫醚;
  硫双二氯酚;
  2,2'-硫代双(4,6-二氯酚);
  2,2'-硫代二(4,6-二氯苯酚);
  2,2-二甲基-7-乙氧基-6-甲氧基-4-色满酮;
  别丁;
  2,2′-硫双(4,6-二氯酚);
  硫氯粉;
  

• 英文名称：

  bithionol

• 英文别名：

  Bitin;
  2,2'-Thio-bis(4,6-dichlorophenol);
  2,2'-Thiobis(4,6-dichlorophenol);
  Bithionolate;
  2,2-DIMETHYL-7-ETHOXY-6-METHOXY-4-CHROMANONE;
  Phenol, 2,2‘-thiobis[4,6-dichloro-;
  2,2’-sulfanediylbis(4,6-dichlorophenol);
  Bitionol;
  Bidiphen;
  2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol;
  2,2’-thiobis[4,6-dichlorophenol];
  Bithionol sulfide;
  bis (2-hydroxy-3,5-dichlorophenyl)-sulphide;
  bis(3,5-dichloro-2-hydroxy phenyl)-sulfide;
  2,2’-thiobis(4,6-dichlorophenol);
  Lorothidol;
  Bithin;
  

• CAS号：

  97-18-7

• 分子式：

  C12H6Cl4O2S

• 分子量：

  356.05200

• 精确质量：

  353.88400

• PSA：

  65.76000

• LogP：

  5.86260

物化性质

• 外观与性状：

  白色或淡灰色-白色,结晶粉末无气味的或带有淡芳香或酚醛气味

• 密度：

  1.61

• 熔点：

  188°C

• 沸点：

  444.7oC at 760 mmHg

• 闪点：

  222.8oC

• 稳定性：

  Stable. Incompatible with strong oxidizing agents.

• 储存条件：

  0-6oC

安全信息

• 危险品标志：

  Xn

• 包装等级：

  II

• 危险类别码：

  R20/21/22

• 海关编码：

  2930909090

• RTECS号：

  SN0525000

• WGK Germany：

  3

• 危险类别：

  6.1(a)

• 安全说明：

  S28-S36/37-S45-S36

• 危险品运输编码：

  UN 2811 6.1/PG 2

生产方法及用途

• 生产方法

  1、以苯酚为原料,先氯化生成2,4-二氯苯酚,然后再用一氯化硫进行硫化生成硫双二氯酚。
  (1)氯化 苯酚与氯反应制得2,4-二氯苯酚:首先将苯酚熔融,在57-63℃通入干燥氯气35h。反应结束后,得到2,4-二氯苯酚。收率可达91.5%左右。 
  (2)硫化 二氯苯酚与一氯化硫在三氯乙烯和无水三氯化铝存在下,反应得硫双二氯酚:在的应罐内依次加入二氯苯酚、三氯乙烯、无水三氯化铝在50±2℃加入一氯化硫,大约2.5h加完,再恒温反应2h。过滤,用三氯乙烯洗涤、烘干,得粗硫双二氯酚。收率可达51.3%左右。 
  (3)精制 在的反应罐内加入粗硫双二氯酚,再加入氢氧化钠溶液,加热溶解后,降温至0℃,加氯化钠,搅拌使之盐析,再加饱和氯化钠溶液,搅拌均匀。静置,过滤,用饱和氯化钠溶液洗涤,回收,得到硫双二氯酚钠。再将其溶于蒸馏水中,经过滤,搅拌加入80℃左右3.5%的盐酸,析出沉淀,静置,分出上层液。沉淀用蒸馏水洗涤至pH值为2,过滤、水洗至pH为7左右,烘干得硫双二氯酚。 
  2、以苯酚为原料经氯化、硫化得硫酸二氯酚。 干燥的氯气通入熔融的苯酚(57-63℃),35h后2,4-二氯酚,收率越91.5%。然后将二氯苯酚、三氯乙烯、无水三氯化铝加入反应釜,于48-52℃下通二氯化硫(SOC
  l2)2.5h,并恒温反应2h。冷却后过滤,用三氯乙烯洗涤,烘干得硫氯酚粗品。粗硫氯酚溶解于热氢氧化钠溶液,冷却后加食盐盐析,用饱和食盐水洗涤得硫氯酚钠。硫氯酚钠溶于水,过滤后加入稀盐酸酸析。静置后滤出沉淀,水洗至中性,烘干得成品。

• 用途

  1.本品用作防菌剂,可作为天然胶乳的保存剂,也有显著的抗凝固作用。既可单独使用,也可与氨并用,一般用量为0.001%以上,经乳化或分散加入胶乳,也可以碱金属或*形式加入胶乳。本品也用于制造驱虫剂,对肺吸虫囊蚴有明显杀灭作用。对姜片虫华支睾吸虫均有效。 
  2.为防菌剂和兽药。可作为天然胶乳的保存剂,经乳化或分散加入胶乳,也可以碱金属或*形式加入胶乳。也有显著的抗凝固作用。既可单独使用,也可与氨并用,一般用量为0.001%以上。对杀灭或病疗肺吸虫囊蚴、姜片虫华支睾吸虫、猪盛许壳绦虫均有效。