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Sorry about the cryptic title.

is a character that can mean "bench"/"desk" but it can also mean "(legal) case" or "file":

  1. 长形的桌子或架起来代替桌子用的长木板:~子。~板。书~。条~。拍~而起。

  2. 提出计划、方法和建议的文件或记录:档~。备~。议~。提~。方~。有~可查。~卷。~牍。

How does this one character come to mean two very different things? The radicals suggest that the original definition may have only been the "bench" one, and the second definition is only incidentally related - I guess people would look at legal cases on a bench or table, but it seems a bit of a stretch.

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1  
So far I don't know any material evidence that can directly answer this question. Possible hints: 1) The earliest historical relic I can find for the character is on 睡虎地秦简 (dating from the late Warring States Period or Qin Dynasty), the seventh slip of 语书: "今且令人案行之" (here 案行 means "perambulation"). 2) For some early records with the character , check this link, you can find in the early times it had already got many meanings (also shown in 汉典's 详细解释 tab of 案). – Stan Jan 22 '14 at 16:06
    
I think your conjecture may be ture, but there's also other possible ones, e.g. 案(table) and 案(case) were derived from different original characters while the original ones are missing today. What's interesting, the noun case also has two different meanings (details can be found on this site). – Stan Jan 22 '14 at 16:07
    
At least they are not completely unrelated. My understanding is that bench/desk -> writing on a desk -> files -> (a lot of meanings but all related to file) – user58955 Jan 23 '14 at 19:59

Your understanding seems to be correct. For example, in Liu Yuxi of Tang Dynasty's 《陋室铭》:

无丝竹之乱耳,无案牍之劳形

Where means the desk, and is a type of hard wood board or pad, on which you write articles. Put together, the bisyllabic word simply means cases, articles, or documents.

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This is interesting but I don't think it shows that 案 gets its "case" meaning in 案牍. For example, in 《答张士然》(written by 陆机(261-303)) there is the passage "终朝理文案,薄暮不遑瞑。" which suggests that 案 picked up this meaning earlier than 《陋室铭》. – congusbongus Jan 22 '14 at 23:00
    
I have no intention of identifying exactly when and from which piece got its second meaning. My answer is more of an illustration of the legitimacy of its alternative usage. – Q. Zhou Jan 25 '14 at 10:34

Q.Z.'s anwser is correct. Allen St.Clair's answer is also right. I don't know why it's downvoted. I have some additions for them

(case) is an extension in meaning of bench. Officials sit around a bench/desk, and deal with their documents. Because Chinese have a "bad habit" -- imagination and association, 案, unfortunately, have had another meaning which is documents/files/cases. (This is reasonable. If you were attacked by aliens and they were driving a UFO which looks like an apple, apples would remind you of the attack every time you see them!)

案 is not the only example of association and imagination. Here comes another example.

Take a look at the 甲骨文 and 金文 of 典 (“典”的字源). The 甲骨文 of 典 looks like a book in hands, read by a man. The 金文 (as well as 小篆) of 典 looks like a book on desk, read by a man. Books in the ancient times are rare and valuable, so only classics can be "printed". That's why 典 means classics.

We can now draw the conclusion: the ambiguity is often caused by active imagination! :-P

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In a courtroom, a "bench" refers to the JUDGE's bench.

In this context, "to bring something to the bench" is to bring something to trial. That "something" is a legal case.

Put another way, a "bench" is where a legal case is filed, which is why they are synonymous.

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A somewhat late suggestion. In Chinese bureaucratic practice, there were specific tables where specific documents where placed. For example, the 奏案 was a table where memorials 奏 to the emperor were put before they were presented.

This evolved into a filing system, where related documents were all kept together on one table. This is parallel to English 'case' where the documents for one particular legal proceeding were kept in separate boxes ("cases").

Instead of a case of documents, though, Chinese has a table of documents. Thus an 案件 is thus simply a document (or documents) from a particular table. Chinese did of course have containers to put this stuff in too. There were 卷宗, which were paper folders for documents (存放文件的紙夾), and 卷帙 which were cases for documents (裝書的套子).

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I think this is the evolution path: 案 means bench at the beginning. People usually put documents and books on bench, to reference the documents put on bench, people created a new word 案牍 for it. 案牍 means "documents on bench", it's the document itself, not the content.

Now, let's imagine. One day, some people sit around a bench, discussing some cases written on 案牍. One man said:

"这个案牍讨论完了, 把那个案牍递给我。"

Here people sit close to each other, the man might just point his finger at the document he wanted, then other people knew what he wanted.

The other day, these people might talking the cases at a different place where they can't see the documents.

"举报赵太守贪污的那个案牍,你们看过了吗?"

Attention! They start to reference the documents with what the content it contains. On the other hand, 案牍 starts to be used to reference the case.

Morden Chinese uses 案件 instead of 案牍 while talking about "case".

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Well. This is very hard to answer because Chinese characters have evolved into different shapes over time. However, if the 案 remains the same shape, we can tentatively guess its meaning.

Take a look at the upper half: it's "安“, which means the security of a town/country, etc. It might be related to some documents and cases.

Take a look at the lower half, it's "木“. You see how it is associated with tables.

If you are a language learner, you don't have to care about it. It's too trivial.

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2  
Swearing is not going to help your case here, please refrain from doing that. – deutschZuid Jan 23 '14 at 0:51
1  
安 is the 声旁, it just indicates the pronunciation. – user2550062 Dec 25 '15 at 7:16

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